The Free Pre-Retirement Quiz asks 10 very important high level questions on your retirement readiness plans.   

The Free Pre-Retirement Quiz is great, but If you feel the need to dive in deeper, here’s a comprehensive list of 100 pre-retirement questions you and your spouse should consider regarding your future retirement life, living situation, finances, health, and family dynamics.

If aligned, check if off.  If not, mark for follow up.

General Retirement Lifestyle

1. What do we want our daily routine to look like after retirement?
2. How do we envision spending our time in retirement?
3. What hobbies or activities would we like to pursue more in retirement?
4. Are there any skills we want to learn or develop in retirement?
5. Do we want to travel? If so, where and how often?
6. What type of home do we want to live in (house, condo, apartment)?
7. Should we downsize or move to a smaller home?
8. Do we want to live in a different city, state, or country?
9. Are we open to living in an age-restricted community or retirement village?
10. Do we want to buy or rent our next home in retirement?
11. Should we consider moving closer to children or grandchildren?
12. What climate do we prefer to live in for our retirement years?
13. Would we consider living part-time in two locations?
14. Are we interested in volunteer work? If so, what type?
15. Do we want to continue working part-time or consulting?
16. What do we want to do to stay active in retirement?
17. How important is having a close social circle in retirement?
18. Should we join clubs, organizations, or groups for retirees?
19. Are we comfortable with technology, and do we want to learn more?
20. How much social interaction do we want in retirement?

Financial Considerations

21. Have we calculated how much money we need to retire comfortably?
22. When do we plan to start drawing Social Security benefits?
23. What will our retirement income sources be (pension, savings, investments)?
24. Should we start a more aggressive savings strategy leading up to retirement?
25. Do we need to update our estate plan and will?
26. Are we familiar with the tax implications of our retirement income?
27. Have we reviewed our retirement accounts and investment portfolios?
28. Should we hire a financial planner or retirement advisor?
29. How much do we plan to spend each year in retirement?
30. How will we handle long-term care or medical expenses?
31. Have we considered the impact of inflation on our retirement income?
32. Do we have enough saved for emergencies or unexpected expenses?
33. Will we have enough money for healthcare, especially Medicare or supplemental insurance?
34. Do we want to leave money for our children, grandchildren, or other heirs?
35. How will we handle debt during retirement, if any?
36. Are we considering any major purchases in retirement (cars, home renovations)?
37. Do we plan to use any retirement savings to fund travel or leisure?
38. Should we consider annuities or other income-generating investments?
39. How do we plan to adjust our budget once we’re retired?
40. Will our retirement lifestyle impact our current spending habits?

Health and Wellness

41. Have we planned for potential healthcare costs in retirement?
42. Should we look into long-term care insurance?
43. How will we ensure that we stay healthy and active in retirement?
44. Are we currently taking steps to improve our health before retirement?
45. How will we manage our healthcare needs if we relocate?
46. Do we need to start seeing doctors more regularly as we approach retirement?
47. Are we prepared for the possibility of needing help with daily activities in the future?
48. Do we have a strategy for dealing with any ongoing health conditions?
49. Have we created an advanced healthcare directive or power of attorney?
50. How will we manage prescriptions or medical treatments in retirement?
51. Do we need to find a new healthcare provider before retiring?
52. Should we get a second opinion on any health issues before retiring?
53. Are we considering joining a fitness class or gym?
54. What wellness routines (yoga, walking, etc.) would we like to incorporate into retirement?
55. Have we set fitness goals for the next few years?
56. Are we prepared for the possibility of one of us becoming seriously ill?
57. Do we have access to resources for mental health or counseling if needed?
58. Are we comfortable discussing health concerns with each other?
59. Should we consider genetic testing or health screenings before retirement?
60. How can we maintain our cognitive health as we age?

Family and Relationships

61. Do we plan on spending more time with family and friends after retirement?
62. How do we want to handle family obligations in retirement (helping children, grandkids)?
63. Should we consider any family caregiving responsibilities?
64. How will we balance our time between each other and our extended family?
65. Are we comfortable with the idea of family members living with us, temporarily or long-term?
66. How do we plan to communicate our retirement plans with family?
67. Should we spend more time nurturing our relationship with each other?
68. What do we want our legacy to be, and how can we pass that on to family?
69. How will we manage any inheritance or estate planning for children or grandchildren?
70. Do we want to participate more in family traditions or create new ones?
71. Are there any family dynamics or potential conflicts to consider before retiring?
72. How can we ensure that we continue to grow as a couple after retirement?
73. Do we want to mentor younger generations or offer them guidance in retirement?
74. Should we plan for family holidays or vacations as part of our retirement schedule?
75. How will we balance independence with being involved in family activities?
76. Should we host family gatherings or reunions more often?
77. How much time do we want to spend with grandchildren (if applicable)?
78. Do we want to consider downsizing to create space for family visits or guests?
79. How will we stay connected to family members who live far away?
80. Should we start writing down family history or stories to pass on to future generations?

Housing and Living Arrangements

81. Will we consider staying in our current home or downsizing?
82. How important is home maintenance after retirement? Are we ready for it?
83. Should we make modifications to our home to accommodate aging?
84. Would we be open to renting a vacation property or part-time home?
85. Are we interested in a senior living community or assisted living?
86. What are the pros and cons of aging in place versus moving to a retirement community?
87. Do we need to create a home maintenance plan for the future?
88. Should we consider moving to a location with better healthcare facilities?
89. Do we want a garden or outdoor space in our retirement home?
90. Should we downsize before retirement to free up cash for travel or other goals?
91. Are there any home renovations we should consider before retiring?
92. Do we want to rent an apartment in a city or town for part of the year?
93. Would we ever consider co-living with others in retirement?
94. How do we feel about homeownership versus renting in retirement?
95. Should we consider buying a property in a different country for part of the year?
96. How will we handle home repairs or upkeep after we retire?
97. Would we like to live in a community with other retirees?
98. Should we move closer to amenities or nature?
99. How do we feel about moving to an urban, suburban, or rural area in retirement?
100. Would we consider giving up a car and using public transportation in retirement?

These questions help both individuals and couples reflect on their future plans, prepare for retirement’s financial, emotional, and physical demands, and align their goals as they transition into this new phase of life.